Rac-(1r,4r)-4-methoxycyclohexane-1-carboxylic acid → (4-Methoxycyclohexyl)methanol

4-Methoxycyclohexanecarboxylic acid (7 g) in tetrahydrofuran (20 mL) was treated with 1 M (in tetrahydrofuran) borane-tetrahydrofuran complex (100 mL) overnight. The mixture was concentrated and the residue was dissolved in methanol (100 mL) and concentrated HCl (10 mL). The resulting mixture was stirred for 1 hour and concentrated. The residue was dissolved in dichloromethane and washed with water. The organic layer was dried over Na2SO4, filtered, and concentrated to give the title compound.

1. concentrationThe mixture was concentrated
2. dissolutionthe residue was dissolved in methanol (100 mL)
3. concentrationconcentrated
4. dissolutionThe residue was dissolved in dichloromethane
5. washwashed with water
6. dry with materialThe organic layer was dried over Na2SO4
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-5c3961683bd646a6a927b0b2f069973e

Source dataset

uspto-grants-2015_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09045475B2